The Best (and Worst) Dressed Men at the 2008 Oscars

A look at the sartorial highlights and lowlights from Oscar night, along with pointers for what to do and not to do at your next black-tie affair.UPDATE: Catch up on the 2009 best dressed men and 2010 best dressed at the Academy Awards!

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Even with a few unexpected wins, last night's Oscars were, shall we say, boring. And most of the men in attendance dressed the part, squirming in their tuxes like their moms picked them out. But the cold and rainy L.A. night also offered a few standouts: experiments in greatness (who knew P. Diddy cleaned up so nice?), cautionary tales (paging Mr. Busey!), and pleasant surprises (Julian Schnabel left his pajamas at home). And, best of all, some lessons on how to make sure you don't pull a Busey at your next formal event.

Super-duper smooth, and believe it or not, he manages to top Clooney as our best dressed for the night. As with last year, Carell is wearing Domenico Vacca. Pay attention at home: This is how it's done.

Superlative. George's last outing was in a tux with a notch lapel. He made a better choice this season. He certainly doesn't feel the need to take chances or insert his personality into his outfit. Classic, simple. Take this picture and show your tailor.

Wearing a tux is easy -- if it fits and you follow the rules, it doesn't take a dandy to look great in one. Hopper is a great example of someone who looks amazing, and by dint of the late '60s and some adventures in psychopharmacology, probably has no idea where he is.

This is the Academy Awards' lowest common denominator. Esquire wants this lazy "Do I have to?" way of dressing stamped out right now. Just because the invite says "black tie" doesn't mean you have to wear one. Remember, dressed like that there's always a chance someone will ask you for more iced water.

Four- and five-button tuxedo jackets are kind of like Javier Bardem's hair in No Country for Old Men -- most people can't pull them off without looking like a pervert or serial killer. But because Javier Bardem is Javier Bardem, and he's wearing Prada, he's able to wear the suit with confidence and make it his own. Lesson: You wear the suit, and if you don't feel like a million bucks, you're not going to look it.

Was it just us, or did Tommy Lee Jones look completely miserable the entire ceremony? And is it also just us, or does his suit totally not fit? Probably about a size too big, and the lapels could use a good steaming.

Number one rule of being a good party guest: If you don't want to go, don't go. Number two: Even if you don't want to go, at least dress like you want to be there.

Probably the same notch lapel (minus 8 points, Sean) tux he wore for Mystic River; nothing wrong with that, per se, but it doesn't really fit, although it might have if he had removed the popcorn from the last time he wore it. Lesson: If it's been a few years since you last wore your tux, try it on a few weeks before the big event and see if it needs any minor alterations. A tailor can make all the difference.

Anyone who's followed Daniel Day-Lewis's red carpet career knows this could've been a lot worse. The shoes, obviously, are a problem -- with a tux, patent leather loafers or formal oxford shoes are the only options -- but otherwise, kudos to Day-Lewis for keeping his freak in check.

The evening coat as tuxedo blazer … very Victorian. Like a lot of things Viggo does, you shouldn't try this at home, but he pulls it off by virtue of being Viggo. We're also big fans of the boutonniere -- not for everyone, sure, but it adds a touch of élan to the outfit.